In the Room with Matt Martin

The Room Podcast
5 min readMay 10, 2024


Unlocking The Future of Scheduling for Every Professional with Matt Martin, Co-Founder of Clockwise

Welcome back to The Room Podcast! This week, we’re excited to sit down with Matt Martin, Co-founder and CEO of Clockwise, a revolutionary productivity platform. Matt shares his career journey, detailing his evolution from tech enthusiast to the founding team of Clockwise, why he founded Clockwise, and his passion for a productivity software that works.

Matt elaborates on Clockwise’s success in providing efficient scheduling solutions by leveraging advanced technology with intuitive design. In our conversation, we explore Clockwise’s approach, using AI to transform time management for professionals and reshaping the way individuals approach their schedules.

In this episode, insights and themes include the importance of mentorship for fueling your growth, knowing when to go from free to paid in a viral product, and changing how we perceive and manage our most valuable resource — time.

Let’s open the door.

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Theme 1: The Importance of Mentorship for Fueling your Growth

Martin gives more credit to the seemingly trite saying that “it’s really the friends you make along the way,” than most people. The phrase came to mind jokingly, but Martin stands by the fact that early introductions in his career accelerated his later ventures far more than he could expect.

Coming to Dartmouth as an undergraduate studying Government from Twin Cities, Minnesota, he started his first professional days as a winter political intern in Washington, D.C. Martin really connected with his coworkers there and asked about ways he could stay in-the-loop all the way from rural Hanover, NH. His senate colleagues encouraged him to start a blog. That foundational experience of building and managing a website in college even rocketed him to moments of unplanned fame. One post from his blog landed his name on the front page of the New York Times.

In his career after graduating from law school in 2010, Martin consistently found that earlier, unexpected relationships would open up opportunities down the line. Having always been fascinated by computers and technology, Martin went to work as a software engineer at RelateIQ, a relationship intelligence platform, in 2014. Later that year, the company was acquired by Salesforce, rebranding it as SalesforceIQ. The RelateIQ founder and CEO Steve Loughlin left the company around the time of the acquisition and became a partner at Accel Ventures. Loughlin, believing in the product Clockwise had to offer, was their first investor soon after Clockwise’s 2016 founding. Relationships built over time with deep trust often come back around in surprising and fortuitous ways.

Theme 2: Knowing When to go from Free to Paid in a Viral Product

Clockwise’s team wanted their product to prove itself in the market, generating momentum from internal team members evangelizing their product to coworkers. By this reasoning, Clockwise only allowed sign-ups with enterprise and business-linked emails, no gmail accounts for personal use. Martin wanted to streamline their go-to-market as a strategy to become so embedded in businesses of significant scale (a notable example, Uber) that “whoever writes checks” would be much more willing to purchase the program business-wide when Clockwise eventually monetized.

Martin expresses some regret over how long their team waited to turn the product from free to paid. They launched Clockwise publicly in 2019, but didn’t begin to ramp up paid versions marketed to companies until 2021, amounting to two free years in the market. However, Martin learned the delay and focus on continuous growth does play directly into the goals for venture-backed startups. Venture investors ultimately want massive scale for a business, which is their means of generating massive VC-level returns. Clockwise’s maniacal focus on those word-of-mouth endorsements over their two years as a free product ultimately was a key to scaled success. With his team able to focus on delivery of the product during that time and continuously updating Clockwise’s features based on feedback, they could use the more than $76 million raised from VCs to push growth before profitability. For other founders considering the decision around monetizing, when to start charging may really depend on the time and focus available from their team to design and implement priced models.

Theme 3: Changing How We Perceive and Manage our Most Valuable Resource — Time

Martin noticed a unifying thread tying countless business people’s complaints together: not having enough time to actually do their job. Given the chance to talk to any number of people working in corporate roles, their calendar — able to be filled up, effectively hijacked — by coworkers at any point during the day controlled their workflow, making periods of focused work hard to come by.

As Martin considered this problem throughout his time as a software engineer and then a manager, he started to think people considered this problem of time in the wrong way. Rather than an individual resource for people to selfishly protect, the persistent calendar issue was a network problem — the type of problem computers are particularly well-suited to address. Clockwise treats calendars within an organization as a network, aggregating individual data to understand the time constraints and needs of a team. Without user input at all, Clockwise’s algorithm is able to move meetings to create efficient schedules for an entire team.

Fielding a question nearly all founders receive when scaling a startup — why is the time now to use natural language models to manage calendars with Clockwise? Martin pulls on examples of competitors that were around in the time Clockwise was founded in 2016. Some aspired to create fully digital automated executive assistants. Many of their peer companies with that mission are no longer around. Martin drills down on the need to “augment and assist” rather than automate and replace, a distinction he says is critical in a time where AI is such a buzzword. The recent improvement of generative AI (“GenAI”) transcends the ability to simply process language, but rather can interpret human intent. The jump from GPT versions 3.5 to 4 alone gives the model a much better temporal sense, which is crucial to Clockwise’s core functions. Clockwise’s next step, Martin says, is building out the product as an assistant native to the visual calendar platform, which customers will be most receptive to. Though trust in extensively trained AI models is improving, most customers want to see where Clockwise is adding and editing in the Outlook or Google Calendar native interface they are accustomed to.

With extensive learnings and know-how from the natural experiment that COVID-19 offered, Martin hopes to continually iterate Clockwise and free more people from a poorly-managed schedule. Where no one can individually “muscle their way” out of a bad schedule, Clockwise is there to help, Martin says.